Approaches to the Synthesis of a Water-soluble Carboxy Nitroxide

Thomas, Komba, Fairfull-Smith, Kathryn E., & Bottle, Steven E. (2013) Approaches to the Synthesis of a Water-soluble Carboxy Nitroxide. European Journal of Organic Chemistry, 2013(5), pp. 853-857.

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The robust and diversely useful isoindoline nitroxide, 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl (1; CTMIO), has previously been synthesised in low-to-moderate yields from phthalic anhydride (3). Recent interest in its biological potential as a potent antioxidant and in other areas has seen an increased demand for its production. Herein, three new synthetic routes to CTMIO are presented and their efficiencies assessed. Two routes, via the nitrile 9 and the formyl compound 11, derive from 5-bromo-1,1,3,3-tetramethylisoindoline (6). The third approach starts from the readily accessible starting material, 4-methylphthalic anhydride (12), and proceeds by a methylarene oxidation with potassium permanganate. The three new approaches yield CTMIO in comparable overall yields (16–18 %); however, the synthetic efficiency is most improved when employing the nitrile intermediate 9.

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4 citations in Scopus
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3 citations in Web of Science®

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ID Code: 58988
Item Type: Journal Article
Refereed: Yes
Keywords: nitroxide
DOI: 10.1002/ejoc.201201551
ISSN: 1434-193X
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500) > Free Radical Chemistry (030501)
Divisions: Current > Research Centres > ARC Centre of Excellence for Creative Industries and Innovation
Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2013 John Wiley & Sons.
Deposited On: 09 Apr 2013 06:48
Last Modified: 08 May 2013 13:31

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